Stretching Pt. 01

I originally posted this story elsewhere many years ago. I've decided to rework the original story to further elaborate on the details, and include the developments of the last several years. This story is every bit true. Although the details can become a little foggy after so many years, the events are accurate to the best of my memory. This story is about growth, both emotionally and physically, and the recognition and development of a life altering fetish. Just to warn you, this story is also about huge dildos, fisting, vaginal stretching, and even body modification to some degree. It borders on the extreme, and is out of the ordinary for most, but I have learned over the years that many enjoy these same fetishes. If this is not your thing, then you do not need to continue reading. This is our journey.

Circa 2000.

Amy is gorgeous. She has beautiful dark hair, dark eyes, olive skin, and the face of a fiery angel. She is very exotic looking and always has the attention of any guy that spots her. At just over 5'3" and about 105 lbs, she is small. She has a petite frame with narrow hips and slender bones, but yet still manages to have a large muscular ass and thighs. She is very fit, with well defined abs, and perky, although small boobs.

I did just fine with the ladies, and avoided a girlfriend at all costs, as I did not want to settle down. That all changed the day I met Amy. There was something magnetic about her, I just wanted to be with her. I was nearly three years older than Amy and was a bit of a slut in college before we met, and she had just ended a relationship, and had only been with a few guys. We first had sex after our sixth date, and it was very good, but like all couples, we needed to learn more about each other. We were pretty much inseparable from that point on. I remember going down on her mostly shaved pussy for the first time and licking her tight little slit and thin pussy lips. She had a playboy model kind of perfectly shaped little pussy, and was a little uncomfortable when I slide my finger in the first time. Gradually she opened up enough after licking and fingering her for a while, and was dripping wet and ready for my cock. I still remember the pop my cock felt as it entered her tight little pussy for the first time. Luckily I was a little drunk, so I lasted longer than I should have. I do not remember how long it lasted, but remember pulling out and shooting my load all over her tight stomach. She did not have an orgasm, and I later found out she had never had a vaginal orgasm before, and had only cum with clitoral stimulation.

From that first day on we were having sex constantly. I got very good at licking her clit with my tongue, and always did so while inserting a finger into her tight pussy, which would bring her to orgasm. One night after licking and fingering her for a while I popped my cock in her and before long we had switched positions and she was on top. Then it came, her first vaginal orgasm. She was amazed that it happened. After that, sex was 2-3 times per day. I learned that she always had stronger orgasms while receiving clit stimulation and insertion at the same time. I also noticed when she was on top and riding me deep that my cock was just long enough so the head would pop into a "new" section in her pussy. It felt like my cock was penetrating something else. Knowing very little about internal female anatomy at the time, I thought I might actually be penetration her cervix. I later would find out that this is pretty much impossible, and that I was actually pushing past her cervix into the deeper part of her pussy called the posterior fornix. Her pussy always gripped my cock tightly and I would have to concentrate like crazy not to cum too quickly. She had such good muscle control she would squeeze and milk my cock without even moving. This would always make me orgasm quickly, and I would often have to get it back up for a second time to please her. Luckily, I was young and this was no problem. I would come up with all kinds of tricks in order not to cum to soon.

I still remember the first night I ever stretched her pussy. We were both pretty drunk one night and while I was pounding her I slid my index finger into her pussy next to my cock. The tightness was amazing, and her being drunk must have relaxed her enough for it to happen.

Amy asked, "Oh my god, what are you doing?"

"My fingers in you too. Do you like it?"

"Mmmm, it kinda hurts but it feels good. Leave it in and fuck me." She responded.

She went wild and was clearly loving the extra girth in her pussy. It wasn't long before we were both cumming. Apparently she was drunker than I thought because the next day she complained that her pussy was sore and said, "We must have had some rough sex last night because I'm sore and I don't really remember what happened." "What did you do to me?"

I said I didn't really remember either, but I could not get it out of my head how crazy she went with her pussy being stretched.

Sex was fun and exciting, but fairly vanilla over the next year. Then, she let me fuck her ass one night while we were both drunk and anal sex became a once in a while thing. She even had an occasional orgasm while I was in her ass. We were now living apart because she had to finish school and I had graduated and was working in the city. I bought her our first sex toy. It was a small vibrator maybe 5 inches long and 1 ½ inch wide. She was a little shocked, but I told her it was for her to use during the week when I was not around. We started incorporating the toy into our sex life and this was the start of a whole new journey.

In the meantime, I started to look at porn online to keep my mind off from that lack of sex. I really started to like the porn with huge cock porn stars. I was amazed that some of these tiny girls could take these monster cocks with ease. Eventually this led to watching girls with huge dildos. Now remember, this was long ago, so there was not the endless amount of material on any fetish or genre available like there is today. I didn't even have high speed internet yet, so downloading a 15 second clip took a few minutes or more. As I got more into the huge dildo porn, I started to fantasize about Amy taking a really big dildo into her tight little pussy.

During this time, Amy had bought herself a new jelly vibrator that was about the size of my cock, but maybe about an inch longer. She brought it to my apartment on her first visit after buying it. Down near the base, it tapered out to a knot that represented the balls, which and was not considered part of the insertable length. I later measured it and found out the ball at the base was oval shaped and 2 inches by 2 ¼ inch.

"I like it, it reminds me of your cock," Amy said. "I have been fucking it while I use the other one on my clit. Do you want to see?"

I watched as she put the other vibrator to her clit to warm herself up and stared to kiss her.

"Put it in now," she said.

I rubbed it around her pussy to lubed it up and felt the pop as it entered her tight little pussy.

"Slowly," She said.

She started to get worked up and I stated to stroke it in and out. I would push it in as far as it would go, about six inches, where it had tapered out to about 2 inches.

"Ouch", she squealed. "It's too deep, it's not supposed to go in that far."

I backed off and removed the vibrator on her clit and replaced it with my tongue. She was going crazy and building to an orgasm. I was using the new toy like my cock and fucking her hard with it.

"I'm gonna cum!" She screamed.

Just as she was about to cum I pushed on the dildo as hard as I could. The thick knot at the base slipped about 1/3 of the way into her pussy, stretching her, and she let out a huge scream as she had a monster orgasm. Her body convulsed and shook on the bed. She closed her legs, forcing my face away from her clit and the dildo out of her pussy. When she finally came back to earth she gazed at me and said, "Oh my god, that was the best orgasm ever."

My cock was dripping wet and I climbed on top of her. My cock slid into her easier than usually after the good fucking she had just gotten from the dildo. There was still the pop feeling, just not as strong as it usually is.

"Go easy," she said. "I'm kinda sore."

I was so worked up I came quickly. Needless to say, she was too sore that night or the next day to have sex.

"Next time, don't push it so far in," she said. "It hurts." From that day on I was hooked and wanted to relive this again and again. It was part the fact that her pussy being stretched so wide was kind of porn star like and slutty, and part that she had such a huge orgasm while doing it. Deep down, I suspected she really like it, but I did not do it again for a few months.